Hydrochloric Acid → Benzothiazol-5-amine

HRID 2300394Notes

Reaction equation

HRID 2300394 reaction equation
Cl[Sn]Cl.Cl.[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[N:13][C:12]=2[CH:16]=1)([O-])=O.[OH-].[Na+]>>[NH2:5][C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[N:13][C:12]=2[CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 3501355-Nitrobenzothiazole

Product 1

HCID 70749Benzothiazol-5-amineYield 89%

Conditions

Temperature
25 °C

Procedure

To a solution of SnCl2 (7.0 g, 8.8 mmol) and 14 mL of con.HCl was added 5-nitrobenzothiazole (0.65 g, 3.6 mmol) in a portion and resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aqueous NaOH and extracted with EtOAc. Combined organic layers were dried over Na2SO4 and concentrated in vacuo yielding an oil (0.47 g, 3.2 mmol, 89%) which was identified as the amine (>95% pure)and subjected to the following reaction without further purification.

Workup

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with EtOAc
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c91020a01d742b18ad485ae24628cd9
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

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